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Revision as of 17:21, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 460112021 of page 2-Mercaptoethanol for the Chem/Drugbox validation project (updated: 'KEGG').  Latest revision as of 09:38, 23 October 2024 edit Citation bot (talk | contribs)Bots5,391,836 edits Removed parameters. | Use this bot. Report bugs. | Suggested by Dominic3203 | Category:Foul-smelling chemicals | #UCB_Category 74/128 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 443314590 | verifiedrevid = 477213767
| Name = 2-Mercaptoethanol | Name = 2-Mercaptoethanol
| ImageFileL1 = 2-Mercaptoethanol.svg | ImageFile1 = 2-mercaptoethanol 200.svg
| ImageSize1 = 170px
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageFile1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Skeletal formula of 2-mercaptoethanol
| ImageFileR1 = 2-mercaptoethanol-3D-vdW.png | ImageName1 = Structural formula of 2-mercaptoethanol
| ImageFile2 = 2-mercaptoethanol-3D-balls.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageFile2_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of 2-mercaptoethanol
| ImageName2 = Ball and stick model of 2-mercaptoethanol
| IUPACName = 2-Sulfanylethan-1-ol{{Citation needed|date = November 2011}}
| PIN = 2-Sulfanylethan-1-ol<ref name=iupac2013_652>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 697 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The prefixes ‘mercapto’ (–SH), and ‘hydroseleno’ or selenyl (–SeH), etc. are no longer recommended.}}</ref>
| OtherNames = 2-Hydroxy-1-ethanethiol{{Citation needed|date = November 2011}}<br />
| SystematicName =
β-Mercaptoethanol{{Citation needed|date = November 2011}}<br />
| OtherNames = 2-Mercaptoethan-1-ol<br />2-Hydroxy-1-ethanethiol<br />β-Mercaptoethanol<br />Thioglycol<br />Beta-merc
Thioglycol{{Citation needed|date = November 2011}}
| IUPACName =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo = 60-24-2 | CASNo = 60-24-2
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem = 1567
| UNII = 14R9K67URN
| PubChem_Ref = {{Pubchemcite|correct|Pubchem}}
| ChemSpiderID = 1512 | PubChem = 1567
| ChemSpiderID = 1512
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 200-464-6
| UNNumber = 2966 | EINECS = 200-464-6
| DrugBank = DB03345 | UNNumber = 2966
| DrugBank = DB03345
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| KEGG = <!-- blanked - oldvalue: C00928 -->
| KEGG = C00928
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = Mercaptoethanol
| MeSHName = Mercaptoethanol
| ChEBI = 41218
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 41218
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 254951 | ChEMBL = 254951
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| RTECS = KL5600000 | RTECS = KL5600000
| Beilstein = 773648 | Beilstein = 773648
| Gmelin = 1368 | Gmelin = 1368
| 3DMet = B00201 | 3DMet = B00201
| SMILES = OCCS | SMILES = OCCS
| StdInChI = 1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2 | StdInChI = 1S/C2H6OS/c3-1-2-4/h3-4H,1-2H2
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DGVVWUTYPXICAM-UHFFFAOYSA-N | StdInChIKey = DGVVWUTYPXICAM-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=2 | H = 6 | S = 1 | O = 1
| Formula = {{Chem|C|2|H|6|SO}}
| MolarMass = 78.133 g mol<sup>−1</sup> | Density = 1.114&nbsp;g/cm<sup>3</sup>
| Odor = Disagreeable, distinctive
| ExactMass = 78.013935504 g mol<sup>−1</sup>
| MeltingPtC = −100
| Density = 1.114 g cm<sup>−3</sup>
| MeltingPtC = −100 | BoilingPtK = 430
| BoilingPtK = 430 | LogP = −0.23
| VaporPressure = 0.76&nbsp;hPa (at 20&nbsp;°C);<br />4.67&nbsp;hPa (at 40&nbsp;°C)
| LogP = -0.23
| pKa = 9.643
| VaporPressure = 100 Pa (at 20 °C)
| pKa = 9.643 | pKb = 4.354
| pKb = 4.354 | RefractIndex = 1.4996
| RefractIndex = 1.4996
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS environment}}
| ExternalMSDS =
| GHSSignalWord = '''DANGER'''
| GHSPictograms = {{GHS corrosion}} {{GHS skull and crossbones}} {{GHS environment}}
| HPhrases = {{H-phrases|301|310|315|317|318|330|410}}
| GHSSignalWord = '''DANGER'''
| HPhrases = {{H-phrases|301|310|315|317|318|330|410}} | PPhrases = {{P-phrases|260|273|280|284|301+310|302+350}}
| FlashPtC = 68
| PPhrases = {{P-phrases|260|273|280|284|301+310|302+350}}
| ExploLimits = 18%
| EUClass = {{Hazchem T}} {{Hazchem N}}
| LD50 = 244&nbsp;mg/kg (oral, rat)<ref name=hazard></ref><br>150&nbsp;mg/kg (skin, rabbit)<ref name=hazard/>
| RPhrases = {{R20/22}}, {{R24}}, {{R34}}, {{R51/53}}
| SPhrases = {{S26}}, {{S36/37/39}}, {{S45}}, {{S61}}
| FlashPt = 68 °C
| ExploLimits = 18%
}} }}
| Section4 = {{Chembox Related | Section4 = {{Chembox Related
| OtherCpds = ]<br /> | OtherCompounds = ]<br />]
]
}} }}
| Section5 =
| Section6 =
}} }}

'''2-Mercaptoethanol''' (also '''β-mercaptoethanol''', '''BME''', '''2BME''', '''2-ME''' or '''β-met''') is the ] with the ] HOCH<sub>2</sub>CH<sub>2</sub>SH. ME or βME, as it is commonly abbreviated, is used to reduce ] and can act as a biological ] by scavenging hydroxyl radicals (amongst others). It is widely used because the hydroxyl group confers solubility in water and lowers the volatility. Due to its diminished vapor pressure, its odor, while unpleasant, is less objectionable than related ]s.

==Production==
2-Mercaptoethanol is manufactured industrially by the reaction of ] with ]. ] and various zeolites catalyze the reaction.<ref name=Ullmann>{{Ullmann|first=Kathrin-Maria |last=Roy |title=Thiols and Organic sulphides |year=2005|doi=10.1002/14356007.a26_767}}</ref>

:]

==Reactions==
2-Mercaptoethanol reacts with ]s and ]s to give the corresponding ]s.<ref>{{cite web|title=1,3-Dithiolanes, 1,3-Dithianes |url=https://www.organic-chemistry.org/protectivegroups/carbonyl/1,3-dithiolanes.htm |publisher=Organic Chemistry Portal |access-date=27 May 2008 |archive-url=https://web.archive.org/web/20080517162047/http://www.organic-chemistry.org/protectivegroups/carbonyl/1%2C3-dithiolanes.htm |archive-date=17 May 2008 |url-status=live }}</ref> This makes 2-mercaptoethanol useful as a ], giving a derivative whose stability is between that of a ] and a ].<ref>{{cite journal |title= Protection (and Deprotection) of Functional Groups in Organic Synthesis by Heterogeneous Catalysis |first1= Giovanni |last1= Sartori |first2= Roberto |last2= Ballini |first3= Franca |last3= Bigi |first4= Giovanna |last4= Bosica |first5= Raimondo |last5= Maggi |first6= Paolo |last6= Righi |journal= Chem. Rev. |year= 2004 |volume= 104 |issue= 1 |pages= 199–250 |doi= 10.1021/cr0200769 |pmid= 14719975 }}</ref>

:]

==Applications==

===Reducing proteins===
Some proteins can be denatured by 2-mercaptoethanol, which cleaves the ] that may form between ] groups of ] residues. In the case of excess 2-mercaptoethanol, the following equilibrium is shifted to the right:

: RS–SR + 2 HOCH<sub>2</sub>CH<sub>2</sub>SH {{eqm}} 2 RSH + HOCH<sub>2</sub>CH<sub>2</sub>S–SCH<sub>2</sub>CH<sub>2</sub>OH

:]

By breaking the S-S bonds, both the ] and the ] of some proteins can be disrupted.<ref>{{cite web |url=http://www.chemicalland21.com/specialtychem/finechem/2-MERCAPTOETHANOL.htm |publisher=Chemicalland21.com |title=2-Mercaptoethanol |access-date=8 October 2006 <!--DASHBot--> |archive-url=https://web.archive.org/web/20061005223640/http://www.chemicalland21.com/specialtychem/finechem/2-MERCAPTOETHANOL.htm |archive-date=2006-10-05 |url-status=dead }}</ref> Because of its ability to disrupt the structure of proteins, it was used in the analysis of proteins, for instance, to ensure that a protein solution contains monomeric protein molecules, instead of disulfide linked ] or higher order ]. However, since 2-mercaptoethanol forms adducts with free cysteines and is somewhat more toxic, ] (DTT) is generally more used especially in ]. DTT is also a more powerful reducing agent with a ] (at pH&nbsp;7) of −0.33&nbsp;V, compared to −0.26&nbsp;V for 2-mercaptoethanol.<ref name="pmid17921203">{{cite journal|author=Aitken CE|author2= Marshall RA, Puglisi JD|title=An oxygen scavenging system for improvement of dye stability in single-molecule fluorescence experiments|journal=Biophys J|volume=94|issue=5|pages=1826–35|year=2008|pmid=17921203|doi=10.1529/biophysj.107.117689|pmc=2242739|bibcode= 2008BpJ....94.1826A}}</ref>

2-Mercaptoethanol is often used interchangeably with ] (DTT) or the odorless ] (TCEP) in biological applications.

Although 2-mercaptoethanol has a higher volatility than DTT, it is more stable: 2-mercaptoethanol's ] is more than 100 hours at ] 6.5 and 4 hours at pH&nbsp;8.5; DTT's half-life is 40 hours at pH&nbsp;6.5 and 1.5 hours at pH&nbsp;8.5.<ref>Yeh, J. I. (2009) "Additives and microcalorimetric approaches for optimization of crystallization" in ''Protein Crystallization'', 2nd Edition (Ed: T. Bergfors), International University Line, La Jolla, CA. {{ISBN|978-0-9720774-4-6}}.</ref><ref>{{cite journal|last=Stevens R.|author2= Stevens L.|author3= Price N.C.|title=The Stabilities of Various Thiol Compounds used in Protein Purifications|journal=Biochemical Education|year=1983|volume=11|issue=2|page=70|doi=10.1016/0307-4412(83)90048-1}}</ref>

===Preventing protein oxidation===
2-Mercaptoethanol and related reducing agents (e.g., DTT) are often included in enzymatic reactions to inhibit the oxidation of free sulfhydryl residues, and hence maintain protein activity. It is often used in enzyme assays as a standard buffer component.<ref>{{Cite journal
| pmid = 3921014
| pmc = 1144764
| year = 1985
| last1 = Verduyn
| first1 = C
| title = Properties of the NAD(P)H-dependent xylose reductase from the xylose-fermenting yeast ''Pichia stipitis''
| journal = The Biochemical Journal
| volume = 226
| issue = 3
| pages = 669–77
| last2 = Van Kleef
| first2 = R
| last3 = Frank
| first3 = J
| last4 = Schreuder
| first4 = H
| last5 = Van Dijken
| first5 = J. P.
| last6 = Scheffers
| first6 = W. A.
| doi=10.1042/bj2260669
}}</ref>

===Denaturing ribonucleases===
2-Mercaptoethanol is used in some RNA isolation procedures to eliminate ] released during cell lysis. Numerous ] make ribonucleases very stable enzymes, so 2-mercaptoethanol is used to reduce these disulfide bonds and irreversibly denature the proteins. This prevents them from digesting the RNA during its extraction procedure.<ref>{{Cite book | author1=Nelson, David R. | author2=Lehninger, Albert L | author3=Cox, Michael | title=Lehninger principles of biochemistry | year=2005 | publisher=W.H. Freeman | location=New York | isbn=0-7167-4339-6 | pages= | url=https://archive.org/details/lehningerprincip00lehn_0/page/148 }}</ref>

===Deprotecting carbamates===
Some ] protecting groups such as ] (Cbz) or allyloxycarbonyl (alloc) can be deprotected using 2-mercaptoethanol in the presence of ] in ].<ref>{{cite journal |last1=Scattolin |first1=Thomas |last2=Gharbaoui |first2=Tawfik |last3=Chen |first3=Cheng-yi |title=A Nucleophilic Deprotection of Carbamate Mediated by 2-Mercaptoethanol |journal=] |date=2022 |volume=24 |issue=20 |pages=3736–3740 |doi=10.1021/acs.orglett.2c01410 |pmid=35559611 |s2cid=248776636 }}</ref>

==Safety==
2-Mercaptoethanol is considered toxic, causing irritation to the nasal passageways and respiratory tract upon inhalation, irritation to the skin, vomiting and stomach pain through ingestion, and potentially death if severe exposure occurs.<ref>{{cite web | title = Material Safety Data Sheet | url = https://www.sigmaaldrich.com/DE/en/sds/sigma/m3148 | publisher = Merck| access-date= 24 September 2023 <!--DASHBot-->}}</ref>

==See also==
* ] (DTT)
* ] (DTBA)
* ]

==References==
<references/>

{{Authority control}}

{{DEFAULTSORT:Mercaptoethanol, 2-}}
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